N-benzyl-N-methyl-2-oxo-2-phenylethanesulfonamide | 774575-92-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-benzyl-N-methyl-2-oxo-2-phenylethanesulfonamide
• 英文别名: N-benzyl-N-methyl 2-oxo-2-phenylethanesulfonamide
• CAS: 774575-92-7
• 化学式: C₁₆H₁₇NO₃S
• 分子量: 303.382
• InChiKey: LBVBSLPYMNVICT-UHFFFAOYSA-N

物化性质

• 沸点：
  478.5±55.0 °C(Predicted)
• 密度：
  1.248±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-benzyl-N-methyl-2-oxo-2-phenylethanesulfonamide 在 2-氯-1-甲基吡啶碘化物 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以75%的产率得到C₁₆H₁₅NO₂S
  参考文献：
  名称：

  Hepatoselectivity of statins: Design and synthesis of 4-sulfamoyl pyrroles as HMG-CoA reductase inhibitors

  摘要：

  4-Sulfamoyl pyrroles were designed as novel hepatoselective HMG-CoA reductase inhibitors (statins) to reduce myalgia, a statin-induced adverse effect. The compounds were prepared via a [3 + 2] cycloaddition of a Munchnone with a sulfonamide-substituted alkyne. We identified compounds with greater selectivity for hepatocytes compared to L6-myocytes than rosuvastatin and atorvastatin. There was an inverse correlation of myocyte potencies and ClogP values. A number of analogs were effective at reducing cholesterol in acute and chronic in vivo models but they lacked sufficient chronic in vivo activity to warrant further development. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.11.124
• 作为产物：
  描述：

  在 溴 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 N-benzyl-N-methyl-2-oxo-2-phenylethanesulfonamide
  参考文献：
  名称：

  二氧化硫介导的多官能磺酰胺和磺酸酯的一锅，三和四组分合成：二氧化硫烯反应的立体选择性研究

  摘要：

  二氧化硫与环氧硅烷或烯丙基硅烷的烯反应生成甲硅烷基亚磺酸盐，可将其溴化（Br 2或NBS）或氯化（NCS或Cl 2）以生产相应的磺酰卤。它们与伯胺和仲胺或醇反应，分别得到相应的磺酰胺和磺酸酯。将二氧化硫异狄尔斯-阿尔德加成到1-氧基或1,3-二氧基-1,3-二烯上会生成两性离子，该两性离子会加到环氧硅烷或烯丙基硅烷中，生成甲硅烷基亚磺酸盐，可将其原位转化为多官能磺酰胺或磺酸酯。这样可以通过一锅，三和四组分方法快速访问复杂的磺酰胺和磺酸酯库。

  DOI：

  10.1021/jo049047j

文献信息

• US7250444B2
  申请人：——

  公开号：US7250444B2

  公开（公告）日：2007-07-31
• Sulfur Dioxide Mediated One-Pot, Three- and Four-Component Syntheses of Polyfunctional Sulfonamides and Sulfonic Esters:  Study of the Stereoselectivity of the Ene Reaction of Sulfur Dioxide
  作者：Laure C. Bouchez、Srinivas Reddy Dubbaka、Māris Turks、Pierre Vogel

  DOI：10.1021/jo049047j

  日期：2004.9.1

  The ene reaction of sulfur dioxide with enoxysilanes or with allylsilanes generates silyl sulfinates that can be brominated (Br2 or NBS) or chlorinated (NCS or Cl2) to produce the corresponding sulfonyl halides. They react with primary and secondary amines or alcohols to give the corresponding sulfonamides and sulfonic esters, respectively. The hetero-Diels−Alder addition of sulfur dioxide to 1-oxy-

  二氧化硫与环氧硅烷或烯丙基硅烷的烯反应生成甲硅烷基亚磺酸盐，可将其溴化（Br 2或NBS）或氯化（NCS或Cl 2）以生产相应的磺酰卤。它们与伯胺和仲胺或醇反应，分别得到相应的磺酰胺和磺酸酯。将二氧化硫异狄尔斯-阿尔德加成到1-氧基或1,3-二氧基-1,3-二烯上会生成两性离子，该两性离子会加到环氧硅烷或烯丙基硅烷中，生成甲硅烷基亚磺酸盐，可将其原位转化为多官能磺酰胺或磺酸酯。这样可以通过一锅，三和四组分方法快速访问复杂的磺酰胺和磺酸酯库。
• Hepatoselectivity of statins: Design and synthesis of 4-sulfamoyl pyrroles as HMG-CoA reductase inhibitors
  作者：William K.C. Park、Robert M. Kennedy、Scott D. Larsen、Steve Miller、Bruce D. Roth、Yuntao Song、Bruce A. Steinbaugh、Kevin Sun、Bradley D. Tait、Mark C. Kowala、Bharat K. Trivedi、Bruce Auerbach、Valerie Askew、Lisa Dillon、Jeffrey C. Hanselman、Zhiwu Lin、Gina H. Lu、Andrew Robertson、Catherine Sekerke

  DOI：10.1016/j.bmcl.2007.11.124

  日期：2008.2

  4-Sulfamoyl pyrroles were designed as novel hepatoselective HMG-CoA reductase inhibitors (statins) to reduce myalgia, a statin-induced adverse effect. The compounds were prepared via a [3 + 2] cycloaddition of a Munchnone with a sulfonamide-substituted alkyne. We identified compounds with greater selectivity for hepatocytes compared to L6-myocytes than rosuvastatin and atorvastatin. There was an inverse correlation of myocyte potencies and ClogP values. A number of analogs were effective at reducing cholesterol in acute and chronic in vivo models but they lacked sufficient chronic in vivo activity to warrant further development. (C) 2007 Elsevier Ltd. All rights reserved.